Shelter Island Holidays from £933

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Your Shelter Island Holiday

Lock in a Shelter Island holiday package that includes everything you need and nothing you don't. Great for views, fishing and nature, consider basing yourself in the neighbourhood of Orient Point. If taking in sights is on the cards during your trip to Shelter Island, check out top attractions like 67 Steps Beach, Railroad Museum of Long Island and Kontokosta Winery. Whatever your travel plans or the size of your budget, organising a tailored Shelter Island holiday is a cinch with Expedia.

Top Shelter Island Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
San Carlos Hotel

San Carlos Hotel

4.5 out of 5
Manhattan
Price was £1,406, price is now £933 per person
£933
per person
17 Aug - 21 Aug
found 1 day ago
Return direct flight included
London (LGW) to New York (JFK)
9.4/10 Exceptional! (1,828 reviews)
Excelente atención al cliente

Reviewed on 3 Jul 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
Price was £3,766, price is now £2,244 per person
£2,244
per person
14 Sept - 19 Sept
found 1 day ago
Return direct flight included
London (LHR) to New York (JFK)
9/10 Wonderful! (1,003 reviews)
5 star perfect place

Reviewed on 2 Jul 2026

Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Save 100% on your flight
Price was £2,363, price is now £1,443 per person
£1,443
per person
19 Sept - 26 Sept
found 14 hours ago
Return direct flight included
London (LGW) to Newark Liberty Intl. Airport (EWR)
7.4/10 Good! (3,239 reviews)
If you want a clean, perfectly functional and surprisingly "cheap" (considering it's New York, that is) hotel room, and you are planning to do most of your sightseeing from the Upper West Side, then you can't beat New York Night Hotel. It also has a history, formerly know as The Monterey Hotel.

Reviewed on 4 Jul 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was £2,733, price is now £1,675 per person
£1,675
per person
11 Sept - 14 Sept
found 1 day ago
Return flight included
Manchester (MAN) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
Atmosphere was amazing. Layout was incredibly unique. Will definitely be returning

Reviewed on 2 Jul 2026

The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
Save 100% on your flight
Price was £2,913, price is now £1,864 per person
£1,864
per person
19 Sept - 26 Sept
found 9 hours ago
Return flight included
London (LON) to New York (JFK)
8.8/10 Excellent! (618 reviews)
Really fabulous location, clean comfortable and spacious room. Nice continental breakfast, easy onsite parking and very helpful and friendly staff. Would absolutely stay again.

Reviewed on 1 Jul 2026

Where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island
A calm river with a boat docked on the right bank, surrounded by lush greenery and trees.

Silver Beach

While Silver Beach may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Crescent Beach and Sunset Beach.

Find hotels in Silver Beach

Shelter Island Beach Holiday

There's nothing that can beat a Shelter Island holiday. Whether you're enjoying refreshing margaritas at a local hot spot or reading your favourite book by the ocean's edge, your trip to Shelter Island is the time to live out your beachy dreams. Many will suggest you stay close to Wades Beach, situated just 1 mile from downtown. However, you'll also discover a fantastic range of Shelter Island holiday deals around Menhadden Lane Beach and Shell Beach, two other well-liked nearby options.

Shelter Island Essential Information

Language
English
Currency
U.S dollars
Population
1,350
Max Temp Winter
4ºC
Max Temp Summer
24ºC
Top Sights
East Hampton Main Beach, Wolffer Estates Vineyard and 67 Steps Beach

Top hotels in Shelter Island

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
8.4/10 Very good! (817 reviews)
"Beautiful room and location!"

Reviewed on 1 Jul 2026

Get rates
Gurney's Montauk Resort & Seawater Spa
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundable
The price is £80 per night from 9 Jul to 10 Jul
£80
9 Jul - 10 Jul
includes taxes & fees
8/10 Very good! (1,005 reviews)
"While the staff were very friendly and helpful. The property itself was like strolling back into 1980. It was not at all what I was expecting to find upon my arrival. Things were clean enough, but very outdated. I will say that the bed was actually very comfortable. The impression I gathered from ..."

Reviewed on 3 Jul 2026

Pier Blue Inn Old Saybrook - Essex
Offshore Montauk

Offshore Montauk

4 out of 5
71 S Emerson Ave Montauk NY
The price is £560 per night from 20 Jul to 21 Jul
£560
20 Jul - 21 Jul
includes taxes & fees
9.2/10 Wonderful! (146 reviews)
"Amazing location to the beach and town. Brand new. All the appliances and amenities were great. The pool area great as well. Currently building a bar/ resturaunt at the pool to be open for next summer Wouldn’t stay anywhere else in Montauk"

Reviewed on 30 Jun 2026

Offshore Montauk
See all 4,741 properties in Shelter Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
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Family Friendly Holidays

Stay near popular Shelter Island attractions

A clear blue sea with a wooden pier extending into the water, a sailboat in the distance, and a person standing in the water.

Wades Beach

10.0/10 (1 review)
Wades Beach offers calm, shallow waters and a broad sandy shoreline perfect for families seeking safe swimming. Lifeguards patrol in summer, and the pavilion provides a comfortable spot to enjoy the tranquil setting.
See properties

Frequently asked questions

How much does a Shelter Island travel package cost?
Starting from just £933, a travel package is your ticket to affordable travel. Customize your Shelter Island trip by choosing from our great range of airfares, hotels and rental cars.
If I'm not able to travel, can I cancel my Shelter Island travel package?
Your situation can change suddenly, so yes, you can. You may be able to cancel or alter your Shelter Island travel package at no cost within 24 hours of booking. For bookings made more than 24 hours ago, you can still cancel or make changes, but your car rental company, hotel or airline may impose a charge. Need more information? Have a look at our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.
How do I get a cheap travel package to Shelter Island?
One of the easiest ways to save cash (and time) is to combine your bookings with Expedia. Flights, hotels, rental cars and activities — we've got everything you need. Pick and choose a combination that suits you and see your savings stack up. Of course, a package deal is never a one-size-fits-all. That's why we offer more than 550 airlines and 1,000,000 properties globally, which lets you customize your Shelter Island holiday.
Does Expedia offer Book Now, Pay Later Shelter Island holidays?
Expedia has joined forces with online lender Klarna to make your next trip easier on your budget. Paying in instalments means you can spread the costs of your next adventure, leaving you with more cash to spend while you're away. Klarna has several payment plans to choose from, so you're sure to find one that fits into your budget. Browse these flexible payment options:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's easy monthly instalment plans. If paying small amounts each month sounds right for you, pick this option during the checkout process.
  • Pay in instalments holidays: Like the idea of paying down your holiday in multiple transactions? Then check out this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the full total upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan from Klarna.

What are the top hotels in Shelter Island?
People heading to Shelter Island often book a room at Waterfront House With Dock And Private Beach or Lovely Shelter Island Cottage With Panoramic Bay Views. You'll find them in Silver Beach. Another happening neighbourhood is Hay Beach. Waterfront House With Dock And Private Beach and Tranquil Resort Style Retreat With Luxury Gunite Pool 2 Min From Sandy Beaches are reputable choices in this part of town.
How far in advance should I book my Shelter Island holiday?
While prices do change, we generally suggest booking your spot as soon as possible. Many international airfares are available on Expedia up to a year in advance. If circumstances have left you booking last minute, you might still be in luck. Cheap tickets to Shelter Island sometimes appear just weeks before departure.
What does an Expedia Shelter Island travel package include?
From flights and hotels to rental cars, Expedia can help you put together a Shelter Island package that's right for you. Holidaying for a while? Consider a hotel, flight and rental car bundle. If your break is short, a hotel and airfare deal could suit you better. Activities can also be added once you've made your booking. Our packages make it easy to plan and save.
What should I know before booking a Shelter Island travel package?
Whether it's adventure or relaxation you're craving, a Shelter Island travel package lets you organise your escape your way. Plus, you'll score great discounts when you combine your hotel with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Shelter Island Expedia travel package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines all over the world. Our travel packages give you the flexibility to take your pick of available flight, hotel or activity options that fit your needs.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.